JP2002097291A - Method of dyeing plastics under high temperature and high pressure - Google Patents
Method of dyeing plastics under high temperature and high pressureInfo
- Publication number
- JP2002097291A JP2002097291A JP2000333874A JP2000333874A JP2002097291A JP 2002097291 A JP2002097291 A JP 2002097291A JP 2000333874 A JP2000333874 A JP 2000333874A JP 2000333874 A JP2000333874 A JP 2000333874A JP 2002097291 A JP2002097291 A JP 2002097291A
- Authority
- JP
- Japan
- Prior art keywords
- dyeing
- bath
- washing
- minutes
- high pressure
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004043 dyeing Methods 0.000 title claims abstract description 42
- 239000004033 plastic Substances 0.000 title claims abstract description 22
- 229920003023 plastic Polymers 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000005406 washing Methods 0.000 abstract description 19
- 239000000986 disperse dye Substances 0.000 abstract description 14
- 239000000975 dye Substances 0.000 abstract description 7
- 230000002829 reductive effect Effects 0.000 abstract description 2
- 238000010137 moulding (plastic) Methods 0.000 abstract 2
- 238000007598 dipping method Methods 0.000 abstract 1
- 238000000465 moulding Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- RYYXDZDBXNUPOG-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;dihydrochloride Chemical compound Cl.Cl.C1C(N)CCC2=C1SC(N)=N2 RYYXDZDBXNUPOG-UHFFFAOYSA-N 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000004696 Poly ether ether ketone Substances 0.000 description 3
- 239000004697 Polyetherimide Substances 0.000 description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000013530 defoamer Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920002530 polyetherether ketone Polymers 0.000 description 3
- 229920001601 polyetherimide Polymers 0.000 description 3
- 229920000306 polymethylpentene Polymers 0.000 description 3
- 239000011116 polymethylpentene Substances 0.000 description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PYVHTIWHNXTVPF-UHFFFAOYSA-N F.F.F.F.C=C Chemical compound F.F.F.F.C=C PYVHTIWHNXTVPF-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 239000011491 glass wool Substances 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920005672 polyolefin resin Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Treatments Of Macromolecular Shaped Articles (AREA)
- Coloring (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】この発明は、プラスチックを高温
高圧の染色浴中で、染色するこによって着色する方法に
関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method of coloring a plastic by dyeing it in a high-temperature and high-pressure dyeing bath.
【0002】[0002]
【従来の技術】従来、プラスチックの染色には、水溶性
系の染色液に染着促進剤を添加する染色方法、又は、溶
剤を含んだ染色液の中で染色する方法、又は、プラスチ
ック自体を改質することによって、染色可能とする方
法、もしくは、染色の前にプラスチックの表面に何らか
の処理を行う方法、又は、ポリカーボネート樹脂につい
ては、100℃〜120℃までの高温高圧によって、
又、ポリオレフィン樹脂については、90℃〜120℃
の高温高圧によって染色する方法があった。2. Description of the Related Art Conventionally, for dyeing plastics, a dyeing method in which a dyeing accelerator is added to a water-soluble dyeing solution, a dyeing method in a dyeing solution containing a solvent, or a plastic itself is used. By modifying, dyeing method, or a method of performing some treatment on the surface of the plastic before dyeing, or, for polycarbonate resin, by high temperature and pressure up to 100 ° C ~ 120 ° C,
For polyolefin resins, 90 ° C to 120 ° C
There was a method of dyeing by high temperature and high pressure.
【0003】[0003]
【発明が解決しようとする課題】これらには、次の様な
欠点があった。 (イ) 水溶性の染色液に染色促進剤を添加する方法、
もしくは、溶剤を含んだ染色液の中で染色する方法につ
いては、プラスチックの表面が変質したり、火災の危険
があり実用には向かない。又、これらの方法では染色が
出来ないプラスチックがある。 (ロ) 高温高圧によって染色する方法については、ポ
リカーボネート樹脂及びポリオレフィン樹脂であるが、
他のプラスチックについては、研究、及び実用化がなさ
れていなかった。本発明は、これらの欠点を除くために
なされたものである。These have the following disadvantages. (A) a method of adding a dye accelerator to a water-soluble dye solution,
Alternatively, the method of dyeing in a dyeing solution containing a solvent is not suitable for practical use because the surface of the plastic is deteriorated and there is a risk of fire. Some plastics cannot be dyed by these methods. (B) Regarding the method of dyeing by high temperature and high pressure, polycarbonate resin and polyolefin resin are used.
Other plastics have not been studied or put to practical use. The present invention has been made to eliminate these disadvantages.
【0004】[0004]
【課題を解決するための手段】プラスチックの成形物
を、分散染料を添加した染色浴に浸漬し、染色浴の温度
を100℃より150℃までの高温高圧にすることによ
って一定時間染色せしめ、染色終了後、洗浄又は、還元
洗浄によって、表面の未固着の染料を脱落せしめ、あと
よく水洗し、乾燥することにより実用的な染色堅牢度を
もったプラスチックを得るものである。この場合のプラ
スチックとは、ポリフェニレンサルファイド樹脂、ポリ
エーテルイミド樹脂、ポリエーテルエーテルケトン樹
脂、ポリメチルペンテン樹脂、エポシキ樹脂、エチレン
と4ふっ化エチレンの共重合樹脂、ポリビニリデンフロ
ライドのプラスチックをさす。染色浴には、分散染料の
みならず、分散染料分散剤、染色均洗剤、PH調整剤、
消泡剤等の薬品を添加することも可能である。染色終了
後の洗浄については、非イオン又は、アニオン系の界面
活性剤、及びソーダ灰あるいは、苛性ソーダ、アンモニ
ア水等のアルカリ剤を添加した洗浄浴によって行い、
又、還元洗浄とは、ハイドロサルファイト、二酸化チオ
尿素等の還元剤と非イオン又は、アニオン系の界面活性
剤、及び、ソーダ灰、苛性ソーダ、アンモニア水等のア
ルカリ剤を含んだ還元洗浄浴であって、非イオン又は、
アニオン系の界面活性剤は、幾らかのアルコール類を含
んだタイプのものが好ましい。又、分散染料は、染色後
の堅牢度の要求によって、耐光性の良い分散染料を使用
することも可能である。染色時間は、任意の時間を選ぶ
ことは可能であるが、好ましくは、20分から30分で
ある。又、洗浄及び還元洗浄の温度及び時間も任意に選
択可能であるが、好ましくは、60℃から95℃までの
温度、及び、5分から20分までの時間である。本発明
は、以上の様な構成よりなるプラスチックの染色方法で
ある。A plastic molded product is immersed in a dyeing bath containing a disperse dye, and the dyeing bath is heated to a high temperature and a high pressure from 100 ° C. to 150 ° C. to be dyed for a certain period of time. After the completion, the unfixed dye on the surface is removed by washing or reduction washing, washed well with water, and dried to obtain a plastic having practical color fastness. The plastic in this case refers to plastics of polyphenylene sulfide resin, polyetherimide resin, polyetheretherketone resin, polymethylpentene resin, epoxy resin, copolymer resin of ethylene and ethylene tetrafluoride, and polyvinylidene fluoride. In the dyeing bath, not only disperse dyes, but also disperse dye dispersants, dye leveling agents, pH adjusters,
It is also possible to add a chemical such as an antifoaming agent. For washing after the completion of dyeing, a nonionic or anionic surfactant, and soda ash or caustic soda, a washing bath to which an alkaline agent such as aqueous ammonia is added,
Reduction cleaning is a reduction cleaning bath containing a reducing agent such as hydrosulfite and thiourea dioxide and a nonionic or anionic surfactant, and an alkaline agent such as soda ash, caustic soda, and ammonia water. And non-ionic or
The anionic surfactant is preferably of a type containing some alcohols. Further, as the disperse dye, a disperse dye having good light fastness can be used depending on the requirement of fastness after dyeing. The dyeing time can be arbitrarily selected, but is preferably from 20 minutes to 30 minutes. The temperature and the time of the washing and the reduction washing can be arbitrarily selected, but preferably the temperature is from 60 ° C. to 95 ° C. and the time is from 5 minutes to 20 minutes. The present invention is a method for dyeing plastic having the above-described structure.
【0005】[0005]
【作用】100℃から150℃までの染色液にプラスチ
ックを浸漬せしめ、20分から30分染色を行う。分散
染料は、プラスチックの表面より内部に拡散浸透するこ
とにより、染色される。次に60℃から95℃までの洗
浄浴又は、還元洗浄浴にて、5分から20分の間、洗浄
又は、還元洗浄を行い、プラヒチックの表面上の未固着
の染料を脱落、もしくは分解する。後、よく水洗乾燥す
る。The plastic is immersed in a dye solution at 100 ° C. to 150 ° C. and dyed for 20 to 30 minutes. The disperse dye is dyed by diffusing into and penetrating from the surface of the plastic. Next, washing or reduction washing is performed for 5 to 20 minutes in a washing bath from 60 ° C. to 95 ° C. or a reducing washing bath to remove or decompose unfixed dye on the surface of the plastic. After that, wash and dry well.
【0006】[0006]
【実施例】以下、本発明の実施例について説明する。 (イ) ポリフェニレンサルファイド樹脂により成形さ
れた長さ3cm、円頭径9mmのボルトを分散染料ダイ
ヤニックスブルーACE1g、アニオン系の分散染料用
分散均染剤、0.5g/l及び消泡剤、0.5g/lを
添加して、350ccとした染色浴中にて、130℃に
て、20分間染色した。染色終了後冷却、水洗する。次
にこのボルトを、二酸化チオ尿素1g/l、非イオン界
面活性剤(アルコール類を含むタイプ)2g/l、ソー
ダ灰1g/lを添加して、350ccとした還元洗浄浴
中にて、80℃にて、15分間還元洗浄する。あと冷
却、水洗後乾燥する。青色に染色によって着色されたポ
リフェニレンサルファイド樹脂製のボルトが得られた。 (ロ) 厚さ3mmたて4cm横1.5cmのポリエー
テルイミド樹脂製の切削成形品を、分散染料ミケトンフ
ァストブラックZ0.5g、アニオン系分散染料均染剤
1g/l、消泡剤0.5g/lを添加して、100cc
とした染色浴中にて、130℃にて30分間染色した。
染色終了後、冷却、水洗を行い、次に二酸化チオ尿素1
g/l、非イオン界面活性剤2g/l、ソーダ灰1g/
lの添加された還元洗浄浴100ccに浸漬し、80℃
で15分間還元洗浄を行った。終了後、冷却、水洗、乾
燥を行い、黒色に染まったポリエーテルイミド樹脂製の
切削成形品を得た。 (ハ) ポリエーテルエーテルケトン樹脂により成形さ
れた、一辺9.5mm厚さ7.5mmの六角ナットを、
ダイヤニックスブラックRSE2g、消泡剤1g/lを
溶解して、150ccとした染色浴中にて、150℃の
温度で20分間染色した。染色終了後、冷却、水洗し
た。次に、この六角ナットを(ロ)の還元洗浄と同様に
還元洗浄を行い、黒色に染色されたポリエーテルエーテ
ルケトン製の六角ナットを得た。 (ニ) たてが1.2cm、横が1cm、奥行きが1.
8cmで厚みが約1mmのキャップ形のポリメチルペン
テン製成形品を、ダイヤニックスブラックRSE6g、
ミケトンファーストブラックZ5g、ダイヤニックスブ
ルーACE3gと90%酢酸1g/l、及び消泡剤1g
/lを添加することによって、360ccとした染色浴
中にて、125℃にて30分間染色した。染色終了後、
冷却、水洗した。これを(イ)と同様の還元洗浄浴中に
て、60℃で15分間還元洗浄を行った。終了後よく水
洗、乾燥して、濃いグレーに染まったポリメチルペンテ
ン製の成形品を得た。 (ホ) たて6cm、よこ3.5cm、厚さ1mmのグ
ラスウール入りのエポキシ樹脂製の板を、カヤロンポリ
エステルエローAULS0.05g、分散染料分散剤1
g/l及び、シリコン系消泡剤0.1g/lを溶解する
ことによって、100ccとした染色浴中にて、130
℃の温度で20分間染色した。染色終了後、冷却、水洗
した。この板を、二酸化チオ尿素1g/l、及びフレー
ク苛性ソーダ1g/l、及び非イオン系界面活性剤2g
/lを添加することによって、100ccとした還元洗
浄浴中にて、100℃の温度にて15分間還元洗浄し
た。終了後冷却、水洗、乾燥し、黄色に染まったグラス
ウール入りエポキシ樹脂の板を得た。 (ヘ) エチレンと4ふっ化エチレンの共重合樹脂製の
直径3cm、厚さ1mm、幅1.5mmのリング形の成
形物を、レゾリンバイオレットFBL200%15g、
分散染料分散剤1g/l、90%酢酸1g/lを溶解す
ることによって、400ccとした染色浴中にて、14
0℃の温度で30分間染色する。染色終了後冷却、水洗
する。その後、(イ)と同様の還元洗浄浴中にて、90
℃で15分間還元洗浄を行う。終了後冷却、水洗、乾燥
して、赤紫色に染色された成形物を得た。 (ト) 直径1cm長さ1.5cmの円柱形のポリビニ
リデンフロライド製の成形物をダイヤニックスエローA
CE1g、分散染料分散剤1g/l、消泡剤0.1g/
lを添加して、100ccとした染色浴中にて130℃
の温度で、20分間染色した。染色終了後冷却、水洗し
た。あと、(イ)と同様の還元洗浄を行うことにより、
黄色に染色された成形物を得た。Embodiments of the present invention will be described below. (A) A bolt formed of a polyphenylene sulfide resin and having a length of 3 cm and a diameter of 9 mm was added to 1 g of a disperse dye Dyanix Blue ACE, a dispersant leveling agent for an anionic disperse dye, 0.5 g / l and a defoamer, Dyeing was performed at 130 ° C. for 20 minutes in a dyeing bath of 350 cc by adding 0.5 g / l. After dyeing, cool and wash. Next, the bolt was added with 1 g / l of thiourea dioxide, 2 g / l of a nonionic surfactant (including alcohols), and 1 g / l of soda ash, and added in a reducing washing bath of 350 cc to obtain 80 g. Wash at 15 ° C. for 15 minutes. After cooling, washing with water and drying. A bolt made of polyphenylene sulfide resin colored by dyeing blue was obtained. (B) A cut product made of a polyetherimide resin having a thickness of 3 mm and a length of 4 cm and a width of 1.5 cm was prepared by mixing 0.5 g of disperse dye Miketone Fast Black Z, 1 g / l of an anionic disperse dye leveling agent, and 1 g of an antifoaming agent. 0.5 g / l and add 100 cc
In a dyeing bath at 130 ° C. for 30 minutes.
After dyeing, cool and wash with water, then thiourea dioxide 1
g / l, non-ionic surfactant 2 g / l, soda ash 1 g /
immersed in 100 cc of the reduced cleaning bath to which
For 15 minutes. After completion, the resultant was cooled, washed with water, and dried to obtain a cut molded product made of a polyetherimide resin dyed black. (C) A hexagonal nut formed of polyetheretherketone resin and having a side of 9.5 mm and a thickness of 7.5 mm,
2 g of Dynix Black RSE and 1 g / l of an antifoaming agent were dissolved and dyed at 150 ° C. for 20 minutes in a dyeing bath of 150 cc. After dyeing was completed, it was cooled and washed with water. Next, this hexagon nut was subjected to reduction cleaning in the same manner as the reduction cleaning in (b) to obtain a hexagon nut made of polyetheretherketone dyed black. (D) Vertically 1.2 cm, horizontal 1 cm, depth 1.
An 8 cm, approximately 1 mm thick, cap-shaped molded product made of polymethylpentene was prepared using Dynix Black RSE 6 g,
Miketone Fast Black Z 5g, Dyanix Blue ACE 3g, 90% acetic acid 1g / l, and defoamer 1g
The dyeing | staining was carried out at 125 degreeC for 30 minutes in the dyeing bath which made 360 cc by adding / l. After staining,
Cooled and washed with water. This was subjected to reduction cleaning at 60 ° C. for 15 minutes in the same reduction cleaning bath as in (a). After completion, the product was washed well with water and dried to obtain a molded product made of polymethylpentene which was dyed dark gray. (E) A glass wool-containing epoxy resin plate having a length of 6 cm, a width of 3.5 cm and a thickness of 1 mm was placed on a Kayaron polyester yellow AULS 0.05 g, a disperse dye dispersant 1
g / l and 0.1 g / l of a silicone-based antifoaming agent were dissolved in a 100 cc dyeing bath.
Stain for 20 minutes at a temperature of ° C. After dyeing was completed, it was cooled and washed with water. The plate was weighed with 1 g / l of thiourea dioxide, 1 g / l of flake caustic soda, and 2 g of a nonionic surfactant.
By adding / l, reduction washing was performed at 100 ° C for 15 minutes in a reduction washing bath adjusted to 100 cc. After completion, the mixture was cooled, washed with water, and dried to obtain a glass wool-containing epoxy resin plate dyed yellow. (F) A ring-shaped molded product having a diameter of 3 cm, a thickness of 1 mm, and a width of 1.5 mm made of a copolymer resin of ethylene and ethylene tetrafluoride was subjected to resolin violet FBL 200% 15 g,
By dissolving 1 g / l of a disperse dye dispersant and 1 g / l of 90% acetic acid, 14 g
Stain for 30 minutes at a temperature of 0 ° C. After dyeing, cool and wash. Thereafter, in the same reduction washing bath as in (a), 90
Perform reduction washing at 15 ° C. for 15 minutes. After completion, the product was cooled, washed with water, and dried to obtain a molded product dyed in reddish purple. (G) A cylindrical molded article made of polyvinylidene fluoride having a diameter of 1 cm and a length of 1.5 cm was made with Dynics Yellow A
CE 1 g, disperse dye dispersant 1 g / l, defoamer 0.1 g /
1 in a dyeing bath at 100 ° C.
At a temperature of 20 minutes. After dyeing was completed, it was cooled and washed with water. Then, by performing the same reduction washing as in (a),
A molded article dyed yellow was obtained.
【0007】[0007]
【発明の効果】塗装による着色では、塗装面の脱落が大
きいプラスチックに対する着色、又は、顔料等による原
料着色の様な多量な生産の必要もなく、プラスチックの
着色が可能である。According to the coloring by coating, the plastic can be colored without the necessity of mass production such as coloring of plastic with a large falling off of a painted surface or coloring of raw materials with pigments or the like.
Claims (1)
色する方法である。1. A method for dyeing a plastic under high temperature and high pressure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000333874A JP2002097291A (en) | 2000-09-25 | 2000-09-25 | Method of dyeing plastics under high temperature and high pressure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000333874A JP2002097291A (en) | 2000-09-25 | 2000-09-25 | Method of dyeing plastics under high temperature and high pressure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002097291A true JP2002097291A (en) | 2002-04-02 |
Family
ID=18809886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000333874A Pending JP2002097291A (en) | 2000-09-25 | 2000-09-25 | Method of dyeing plastics under high temperature and high pressure |
Country Status (1)
| Country | Link |
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| JP (1) | JP2002097291A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106192486A (en) * | 2016-08-23 | 2016-12-07 | 天津市旭辉恒远塑料包装股份有限公司 | A kind of dyeing and printing process of plastic |
| US20220389652A1 (en) * | 2016-11-07 | 2022-12-08 | Milliken & Company | Textile materials containing dyed polyphenylene sulfide fibers and methods for producing the same |
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2000
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106192486A (en) * | 2016-08-23 | 2016-12-07 | 天津市旭辉恒远塑料包装股份有限公司 | A kind of dyeing and printing process of plastic |
| US20220389652A1 (en) * | 2016-11-07 | 2022-12-08 | Milliken & Company | Textile materials containing dyed polyphenylene sulfide fibers and methods for producing the same |
| US11987929B2 (en) * | 2016-11-07 | 2024-05-21 | Milliken & Company | Textile materials containing dyed polyphenylene sulfide fibers and methods for producing the same |
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